18. Aimee Mann, Bachelor No. 2 (Superego, 2000)

This was the first album I'd ever purchased from an artist's website because you could do so weeks before you could buy it in stores. After two frankly amazing albums (plus the career-reviving Magnolia soundtrack, which slyly previewed a few gems from this one), I dearly hoped that Mann could pull off a triple play, and this solid, sterling set more than did the job. It’s as cunning and cutting as ever: "How Am I Different" and "Nothing Is Good Enough" continue and perfect that failed relationship = faltering career vibe omnipresent in her work, while "Ghost World" almost captures the ennui of Daniel Clowes' comic as well as Terry Zwigoff's great film would a year later. But Bachelor also suggests that Mann’s now listening to Bacharach (she even name-checks him on “It Takes All Kinds”) as much as the Beatles. Songs like “Satellite”, “Red Vines” and “You Do” come across as the perfect blend of those two primary influences, but Mann retains such a singular, witty voice that the results remain distinctly hers.